4-Fluorophenylboronic acid → HCID 11358168, compound

HRID 2106394Notes

Reaction equation

HRID 2106394 reaction equation
C(OC([N:8]1[CH:17]([CH3:18])[CH2:16][C:15]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[N:13]([CH:19]([CH3:21])[CH3:20])[N:14]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.FC1C=CC(C2N(C(C)C)N=C3C=2CC(C)NCC3)=CC=1>>[F:30][C:31]1[CH:36]=[CH:35][C:34]([C:12]2[N:13]([CH:19]([CH3:20])[CH3:21])[N:14]=[C:15]3[C:11]=2[CH2:10][CH2:9][NH:8][CH:17]([CH3:18])[CH2:16]3)=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 2856454-Fluorophenylboronic acidHCID 59752674HCID 59752674, compoundHCID 86598398HCID 86598398, compound

Product 1

HCID 11358168HCID 11358168, compound

Procedure

The title compound (127 mg) was prepared as in Example 311 using 260 mg of 2-isopropyl-7-methyl-3-trifluoromethanesulfonyloxy-4,5,7,8-tetrahydro-2H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester and 115 of 4-fluorophenylboronic acid. The reaction sequence also yielded 3-(4-fluoro-phenyl)-2-isopropyl-5-methyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene. MS (ESI): exact mass calculated for C17H22FN3, 287.18; found, m/z 288.5 [M+H]+. 1H NMR (600 MHz, CD3OD): 7.39-7.37 (m, 2H), 7.32-7.28 (m, 2H), 4.36 (m, 1H), 3.61-3.56 (m, 1H), 3.50-3.47 (m, 1H), 3.20-3.08 (m, 3H), 2.85-2.80 (m, 1H), 2.73-2.69 (m, 1H), 1.46 (d, J=6.6 Hz, 3H), 1.41-1.38 (m, 6H).

Sources & evidence

ORD record
ord-7a03c4b7ffe64c5188de3741d555f269
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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